(+)-1-(1-Naphthyl)ethylamine → (1R)-1-(1-naphthyl)-N-({1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}methyl)ethanamine

HRID 2194845노트

반응식

HRID 2194845 반응식
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11]([CH:14]=O)=[N:10]2)=[CH:5][CH:4]=1.[C:18]1([C@H:28]([NH2:30])[CH3:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.ClCCCl>[C:18]1([C@H:28]([NH:30][CH2:14][C:11]2[CH:12]=[CH:13][N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=3)[N:10]=2)[CH3:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 3

HCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 574169821-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde

생성물 1

HCID 25263532(1R)-1-(1-naphthyl)-N-({1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}methyl)ethanamine

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 111,2-Dichloroethane용매

실험 절차

A 20 mL vial was charged with 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde 65 (0.200 g, 0.833 mmol), (R)-1-(naphthalen-1-yl)ethanamine 39 (0.171 g, 0.999 mmol), sodium triacetoxyborohydride (0.353 g, 1.67 mmol), 4 mL of DCE, and 3 drops of AcOH. This mixture was stirred overnight at room temperature and then quenched with saturated aqueous NaHCO3. The mixture was extracted with DCM, dried, and concentrated. Purification by column chromatography on silica gel (10% to 50% EtOAc in hexanes) gave ((1R)-1-(1-naphthyl)-N-({1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}methyl)ethanamine 66. Mass spectrum, calculated for C23H20F3N3 395.2; found 396.2 (M++1).

후처리

  1. customquenched with saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with DCM
  3. customdried
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (10% to 50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-3f8fd0c45eec4de28e493b15f9747047
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334317B2

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